Hydrochloric Acid → (7-{[Tert-butoxycarbonyl-(2-fluoro-ethyl)-amino]-methyl}-2-chloro-naphthalen-1-yl)-acetic acid
Reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:31])[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20][CH2:21][F:22])[CH:16]=2)[CH:11]=[CH:10][C:9]=1[Cl:30])C.Cl>O1CCOCC1.CO.O>[C:26]([O:25][C:23]([N:19]([CH2:18][C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][C:9]([Cl:30])=[C:8]2[CH2:7][C:6]([OH:31])=[O:5])=[CH:13][CH:14]=1)[CH2:20][CH2:21][F:22])=[O:24])([CH3:29])([CH3:27])[CH3:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 45 °C
Procedure
A aqueous solution of NaOH (2 M, 0.59 ml, 1.17 mmol) was added at RT under an atmosphere of argon to a solution of (7-{[tert-butoxycarbonyl-(2-fluoro-ethyl)-amino]-methyl}-2-chloro-naphthalen-1-yl)-acetic acid ethyl ester (249 mg, 0.59 mmol) in dioxane (2.7 ml). The slightly turbid mixture is rendered clear by the addition of 6 drops of MeOH. After warming to 45° C. for 2.5 h, HPLC analysis indicated complete consumption of starting material. Removal of solvent yielded a residue, which was taken up in water. After acidification to pH 4 by the addition of 1 M HCl, the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was used directly in the next step. ES+-MS: 413.3, 415.5 [M+H+H2O]+. ES−-MS: 394.2, 396.2 [M−H]−.
Workup
- customconsumption of starting material
- customRemoval of solvent
- customyielded a residue, which
- extractionthe mixture was extracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ed28d68328294c3c96a8e0baec8cfcc2
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426440B2
Reaction notes
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